The studies of both e-learning and innovative application of digital material in teaching are flourishing in recent years. This paper offers another way to look at the contents design of literature digitization. This case illustrates the processes of literature digitization for literary texts rewriting and multimedia script making. Development and Production of Digital Learning Contents for Taiwanese Literature, which is promoted by National Museum of Taiwan Literature in 2013, plans to provide three kinds of course content according to the target audience. Considering the differences regarding learning objects and literary genres, course design varies, requiring heterogeneity in the conversions of source to digitalized material. In order to elaborate the whole conversion process of literary texts, this paper is divided into four main sections. Section 1 is the articulation of storyline. For creating amazing storyboard, the novel must be re-structured and poems composed upon a storyline. Section 2 is the creation of images from words with online games, movies, archival photos and other interdisciplinary resources to form the concept map. Section 3 is the compiling of further reading. To make connections across literature and life, the historical knowledge, geographical landscape, and even popular culture that literary curriculum related are integrated in this stage. Section 4 is the design of assessment. In addition to choice-based assessment, there can be open questions in general public version; questions related to the entrance examination in secondary school version, and interactive games for elementary version to add interest. In a word, this paper accentuates the challenges to convert literary material for three types of audience and the factors to successfully communicate with technical professionals.